Title: 10 Best Hotels in Montclair Colony, Shelter Island for 2025 | Expedia.ca

 

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# Hotels in Montclair Colony, Shelter Island

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## Go beyond your typical stay in Montclair Colony

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=SPA_ON_SITE)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&travelerType=family_friendly)

Ocean view

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=OCEAN_VIEW)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=POOL)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=HOT_TUB)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=APARTMENT)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=PETS)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=COTTAGE)

Waterpark

[](https://www.expedia.ca/Hotel-Search?destination=Montclair+Colony%2C+Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=553248635976473165&latLong=41.04996%2C-72.348506&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=WATER_PARK)

## Check prices for these dates

Tonight

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976473165&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976473165&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976473165&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976473165&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Montclair Colony hotels and places to stay

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a48f4b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pier Blue Inn Old Saybrook - Essex

26.7 km from Montclair Colony

8.0/10

Very good

(1001)

"Always a great stay at Pier Blue. Comfy bed and plenty of room."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patricia

CA $112

CA $128 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/770255ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/65651fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/8957afe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Saybrook Point Resort & Marina

25.9 km from Montclair Colony

9.4/10

Exceptional

(1005)

"Beautiful property, we loved our room, friendly staff. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Natalie

CA $331

CA $416 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/e64d0e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/cd124626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/783d70b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Preston House & Hotel

29.7 km from Montclair Colony

9.8/10

Exceptional

(366)

"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nakia

CA $247

CA $283 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information)

![Deluxe Double Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/e3ee1fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room | Private kitchenette](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/b36c7eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/ff8b5175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Bays Hotel on Main

24.1 km from Montclair Colony

7.0/10

Good

(65)

"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Olivia

[](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, sauna, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/533d1f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/5c6281d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa, Multiple Beds, Ground Floor (by the Sea) | Beach/ocean view](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/25adc215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Water's Edge Resort & Spa

26.8 km from Montclair Colony

8.8/10

Excellent

(1011)

"We love the stay everything was perfect"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

angelica

CA $275

CA $340 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information)

![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/511d84f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Old Saybrook - Westbrook

29.9 km from Montclair Colony

7.8/10

Good

(1010)

"Everything was good, had a quiet happy stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aishwariya

CA $130

CA $150 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Harbor View Balcony Junior Suite | Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/e407cc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

5.9 km from Montclair Colony

8.8/10

Excellent

(526)

"Beautiful view and room. Staff friendly and accommodating. Excellent location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John

CA $207

CA $305 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/8ac8989f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/7e8d204d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/ad4e87dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/f50958a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Liberty Inn

29.2 km from Montclair Colony

7.4/10

Good

(637)

"Great little place to stay with friendly staff and clean room"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carolan

CA $102

CA $118 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Old-Saybrook-Hotels-Liberty-Inn.h3004551.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/39934cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/f4e648ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Econo Lodge Inn & Suites Old Saybrook Westbrook

26.8 km from Montclair Colony

7.2/10

Good

(457)

"the so-called breakfast was absolute minimum only thing available was make your own waffle"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brian

CA $100

CA $115 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/003f8776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/b833807a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/1bf554ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Place Long Island East End

29.7 km from Montclair Colony

9.2/10

Wonderful

(1004)

"Loved this hotel. Rooms were spacious and clean and the area is very quaint!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan

CA $188

CA $215 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/806c49e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/55438f97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Honeymoon Room, Jetted Tub](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/5fc9f561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Atlantic Hotel

19.3 km from Montclair Colony

7.2/10

Good

(962)

"Love the area love the room size clean parking was perfect "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sherwood

[](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/9ab5b9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d45c604d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7bb1af0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clinton Motel

28.6 km from Montclair Colony

8.6/10

Excellent

(289)

"Great staff and clean rooms"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyler

CA $109

CA $125 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/deb420de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite, 1 King Bed, Bathtub, Ocean View](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/0c2eed31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Penthouse, 1 Bedroom, Beach View, Executive Level | Garden view](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/ad6abc60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/d87ef3a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aqua by American Beech - Adults Only

24.7 km from Montclair Colony

9.4/10

Exceptional

(311)

"This was our third time staying here. The rooms are clean, the property is quiet, and the view is tranquil. The only way they could be better is getting more partnerships with local businesses and advertising them to guests before their stay (e.g. an email digest) to help guide those who book early."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lindsay

[](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech.h24081913.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/46915263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/22d95002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/865dda17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/f2c9a8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Westbrook Inn B&B

27.4 km from Montclair Colony

9.8/10

Exceptional

(173)

"Charming, beautiful inn; excellent food and service."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael

CA $303

CA $337 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/f0f56ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/dc6eb455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/5b2ed019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Menhaden

5.9 km from Montclair Colony

9.6/10

Exceptional

(168)

"Hotel manager was great! Loved the firepits outside "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa

CA $431

CA $548 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information)

![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/04aa4e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hamlet Inn

20.2 km from Montclair Colony

8.6/10

Excellent

(433)

"A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle

CA $149

CA $193 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/942c49f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/dc9e5678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

6.1 km from Montclair Colony

9.2/10

Wonderful

(282)

"Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Phyllis

[](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![IPod dock, MP3 dock](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/497076d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Bedroom, Private Bathroom](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/bce7c7c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/ab015163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/5ebf0e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Captain Stannard

27.4 km from Montclair Colony

9.6/10

Exceptional

(253)

"Amazing stay! Everything was perfect and it is clear that the owners love their jobs and their inn. Can't wait to go back! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julie

[](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information)

![Studio Unit Upper Oceanfront 'San Remo'  | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lower 2 Bedroom 2 Bath Corner Oceanfront | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5d8554d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Kitchen, Pool View](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/d576d9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 3 Bedrooms, 2 Bathrooms, Ocean View | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/4119983f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sea Crest Resort

27 km from Montclair Colony

9.2/10

Wonderful

(498)

"Perfect location!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bernadette

CA $253

CA $319 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information)

![Beach bar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio | View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/8f5285b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/65a8ebbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/c930d525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Motel & Beach Bungalows

5.5 km from Montclair Colony

9.8/10

Exceptional

(137)

"amazing stay, very quaint and relaxing "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

rebecca

[](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=553248635976473165&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Hotels in Montclair Colony with free breakfast

![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/7564e116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/509e7634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/65f0ee8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shorewood Inn

23.2 km from Montclair Colony

-   Breakfast included
    

8.6/10

Excellent

(702)

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&selected=15241380&PinnedHotelID=15241380&HadPinnedHotel=true&regionId=553248635976473165&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/511d84f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Old Saybrook - Westbrook

29.9 km from Montclair Colony

-   Breakfast included
    

7.8/10

Good

(1010)

CA $130

CA $150 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=3988&PinnedHotelID=3988&HadPinnedHotel=true&regionId=553248635976473165&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/ec2d268d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bentley Hotel Southampton

19.9 km from Montclair Colony

-   Breakfast included
    

9.6/10

Exceptional

(365)

CA $180

CA $206 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&selected=53962986&PinnedHotelID=53962986&HadPinnedHotel=true&regionId=553248635976473165&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/43997189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sound View Greenport

6.5 km from Montclair Colony

-   Breakfast included
    

8.6/10

Excellent

(584)

CA $281

CA $389 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&selected=15273178&PinnedHotelID=15273178&HadPinnedHotel=true&regionId=553248635976473165&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Outdoor pool](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/f95ca887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Building design](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/d11f2952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sag Harbor Inn

6.7 km from Montclair Colony

-   Breakfast included
    

9.4/10

Exceptional

(561)

CA $262

CA $300 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=26497858&PinnedHotelID=26497858&HadPinnedHotel=true&regionId=553248635976473165&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/003f8776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/b833807a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/1bf554ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Place Long Island East End

29.7 km from Montclair Colony

-   Breakfast included
    

9.2/10

Wonderful

(1004)

CA $188

CA $215 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=4258052&PinnedHotelID=4258052&HadPinnedHotel=true&regionId=553248635976473165&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=553248635976473165&adults=2&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true)

## Hotels in Montclair Colony with a pool

![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/4db6535f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/9d3a1088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Master Guest Room](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/90421aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/6809b461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton Art House Bed & Breakfast

15.8 km from Montclair Colony

-   Pool
    

9.6/10

Exceptional

(65)

CA $530

CA $605 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=31007589&PinnedHotelID=31007589&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Graybarn Cottage | Room amenity](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1d639007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Graybarn Cottage | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1f2aee03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/f6e6bd4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mill House Inn

16.7 km from Montclair Colony

-   Pool
    

9.0/10

Wonderful

(70)

CA $453

CA $570 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=2861838&PinnedHotelID=2861838&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/59e33701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/14ba9bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/6b2173cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/d8406ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftwood Resort

27.4 km from Montclair Colony

-   Pool
    

9.0/10

Wonderful

(235)

CA $261

CA $344 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&selected=4207142&PinnedHotelID=4207142&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6d8b086b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Cottage | Private kitchen](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/4648b1d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Suite](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/9bf97ebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Inn and Cottages

22.4 km from Montclair Colony

-   Pool
    

9.8/10

Exceptional

(58)

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&selected=83519458&PinnedHotelID=83519458&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Studio Unit Upper Oceanfront 'San Remo'  | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lower 2 Bedroom 2 Bath Corner Oceanfront | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5d8554d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Kitchen, Pool View](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/d576d9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 3 Bedrooms, 2 Bathrooms, Ocean View | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/4119983f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sea Crest Resort

27 km from Montclair Colony

-   Pool
    

9.2/10

Wonderful

(498)

CA $253

CA $319 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=5232838&PinnedHotelID=5232838&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Outdoor pool](https://images.trvl-media.com/lodging/28000000/27200000/27194600/27194600/565bdaee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27200000/27194600/27194600/1cf4e6bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27200000/27194600/27194600/bca4c06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/28000000/27200000/27194600/27194600/573c5e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A Room At The Beach

13.1 km from Montclair Colony

-   Pool
    

9.2/10

Wonderful

(92)

CA $459

CA $524 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=27194600&PinnedHotelID=27194600&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/acd2c1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/c353f8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/7c3abc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/d697dbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Journey East Hampton

18.2 km from Montclair Colony

-   Pool
    

9.0/10

Wonderful

(154)

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&selected=23252049&PinnedHotelID=23252049&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/d84c46bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/3f4839f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Single Beds | View from room](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9125969a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Topping Rose House

13.1 km from Montclair Colony

-   Pool
    

9.2/10

Wonderful

(135)

CA $609

CA $701 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&selected=5581380&PinnedHotelID=5581380&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/ea3c7561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/84e7ebf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Traditional Cottage, 2 Bedrooms, Lake View](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/45454390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Traditional Cottage, 2 Bedrooms, Lake View | Living area](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/6833ca01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Head of Pond House

14.9 km from Montclair Colony

-   Pool
    

10/10

Exceptional

(2)

CA $734

CA $839 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=112907611&PinnedHotelID=112907611&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

![Deluxe Studio | Living area](https://images.trvl-media.com/lodging/5000000/4230000/4223700/4223615/1ad86f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio | Living area](https://images.trvl-media.com/lodging/5000000/4230000/4223700/4223615/facf84c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio](https://images.trvl-media.com/lodging/5000000/4230000/4223700/4223615/6becca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, Kitchen](https://images.trvl-media.com/lodging/5000000/4230000/4223700/4223615/5de2da62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton House Resort

17.6 km from Montclair Colony

-   Pool
    

9.0/10

Wonderful

(285)

CA $226

CA $288 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=4223615&PinnedHotelID=4223615&HadPinnedHotel=true&regionId=553248635976473165&adults=2&amenities=POOL&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=553248635976473165&adults=2&sort=RECOMMENDED&amenities=POOL&openPlayBack=true)

## Top guest rated hotels in Montclair Colony

![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/1891e70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/e61ec435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/f09f38b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### James Pharmacy Bed & Breakfast

26.4 km from Montclair Colony

9.2/10

Wonderful

(20)

CA $421

CA $468 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=78191036&PinnedHotelID=78191036&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite | Living area](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/767aee45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/52855a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/9091cefd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### American Beech Hotel

6.1 km from Montclair Colony

8.8/10

Excellent

(194)

CA $333

CA $436 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=11951124&PinnedHotelID=11951124&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/67db121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/3e8af6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d269b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room 4, King Bed](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/bf954008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The 1770 House Restaurant & Inn

16.7 km from Montclair Colony

9.8/10

Exceptional

(159)

CA $411

CA $562 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=1085655&PinnedHotelID=1085655&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![Garden](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/98e9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/e5f6999f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free continental breakfast on weekends](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/062f5fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/553f589d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Huntting Inn

16.8 km from Montclair Colony

9.0/10

Wonderful

(104)

CA $533

CA $623 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&selected=35373712&PinnedHotelID=35373712&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/3084ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/620f075e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/8059ee4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, Frette Italian sheets, premium bedding, blackout drapes](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/587cd5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chequit

3.8 km from Montclair Colony

9.0/10

Wonderful

(37)

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&selected=67569836&PinnedHotelID=67569836&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/b8adcc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/c6fa26de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/06408853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bicycling](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/65a49724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Roundtree, Amagansett

19.2 km from Montclair Colony

9.8/10

Exceptional

(89)

CA $968

CA $1,161 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=10547745&PinnedHotelID=10547745&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![Garden Suite King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boardwalk Suite | Private kitchen](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/1898cf3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/81035eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shoals Suites and Slips

5.5 km from Montclair Colony

9.6/10

Exceptional

(218)

CA $235

CA $304 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=76716269&PinnedHotelID=76716269&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![View from property](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/d7311f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/8cc5044d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/fdb9f048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### House on Chase Creek

3.5 km from Montclair Colony

9.4/10

Exceptional

(78)

CA $258

CA $295 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=12610909&PinnedHotelID=12610909&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![Property entrance](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/f0f56ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/dc6eb455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/5b2ed019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Menhaden

5.9 km from Montclair Colony

9.6/10

Exceptional

(168)

CA $431

CA $548 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=35229370&PinnedHotelID=35229370&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

![Aerial view](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/7d31a3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, free beach shuttle, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/05958fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/51a7b673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, brunch served; local cuisine ](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/57a0a6ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Southampton Inn

18.8 km from Montclair Colony

8.6/10

Excellent

(546)

CA $279

CA $341 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=117135&PinnedHotelID=117135&HadPinnedHotel=true&regionId=553248635976473165&adults=2&guestRating=35&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=553248635976473165&adults=2&sort=RECOMMENDED&guestRating=35&openPlayBack=true)

## Where to stay in Montclair Colony

Find the best Montclair Colony areas and neighborhoods for the activities you enjoy most.

-   Coecles Harbor
-   Menantic Creek
-   Silver Beach
-   Shorewood
-   Hay Beach

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976480820)

![Coecles Harbor map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:ybxyFxymxLw%5Das%40rjAyyBnqA%7Cx%40pIl%7E%40%7DhCnt%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=xFWty9iq-ZDYNo-RgTcjrckcozE=)

### Coecles Harbor

When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Sunset Beach, some noteworthy sights in the nearby area.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976480820)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976481214)

![Menantic Creek map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:q%7BryFh%7CqxLeOkr%40fT_EnMqEjKc%40fGjBhAuArItErIPrBnB%7DAb%5Cm_AnW&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=wL_I5E54rllE0bcZHkxAdQylRUE=)

### Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Crescent Beach.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481214)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976481903)

![Silver Beach map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:mzpyF%60vvxLg%60%40kEi%40%7DHuLaYrBOSaK_Oib%40n%40cFuWiStCmEvBXxDwDfHH%7EK%60NpNxDjFyGlHrAf%5CwSlg%40oUhImBpAvPoN%7El%40kp%40dsAcAxK&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=LI215i5nbJyDKLk8XZgKcAhItxY=)

### Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481903)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976481937)

![Shorewood map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:iepyFdhnxLeP%7DEwBi%5Cha%40wNvL%7BLRhb%40cTnSsE%60I&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=qbvaos58sMF0pgaReQcoKBoiPaw=)

### Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481937)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976470037)

![Hay Beach map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:q%7DyyFvxoxLu%7B%40aS%7Ei%40owAnj%40cEfEdc%40a_%40nmA&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=oUw1-B9agSYZdTPReexAj0cx418=)

### Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976470037)

## Top Montclair Colony Hotel Reviews

![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"The staff was beyond helpful and nice, the rooms are huge and clean. Would definitely recommend "

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg)

### The Atlantic Hotel

10/10 Excellent

"Perfect "

[](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg)

### Sound View Greenport

10/10 Excellent

"Beautiful Long Island Sound and sunset views."

[](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![The Harbor Front Inn](//images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg)

### The Harbor Front Inn

10/10 Excellent

"Beautiful view and room. Staff friendly and accommodating. Excellent location. "

[](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"Everything was good, had a quiet happy stay."

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg)

### Zey Hotel

10/10 Excellent

"Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional."

[](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![The Sagaponack](//images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg)

### The Sagaponack

10/10 Excellent

"An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. "

[](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information)

![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Always a great stay at Pier Blue. Comfy bed and plenty of room."

[](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Sag Harbor Inn](//images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf_y.jpg)

### Sag Harbor Inn

10/10 Excellent

"We had lovely stay, the staff was knowledgeable, efficient, and friendly. Will visit again! "

[](https://expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

## Frequently asked questions

### What is Montclair Colony like?

> You'll be sure to have fun visiting Shelter Island's Montclair Colony neighborhood.

### If I need to cancel my hotel reservation in Montclair Colony, will I receive a refund?

> Yes, the majority of hotel room reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it might still be possible to cancel it and get a refund within a 24-hour period of your booking. Enter dates in and click on "Search", then use the "fully refundable" filter to get the best deals available in Montclair Colony.

### What is there to do around this Shelter Island neighborhood?

> A few places to visit in the area around Montclair Colony include Shell Beach, Wades Beach, and Shelter Island Historical Society. When you're sightseeing in Shelter Island, Havens House and Sylvester Manor are also worth a stop.

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-   [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

-   [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
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-   [Visit Sag Harbor](https://www.expedia.ca/Sag-Harbor.dx154327)
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